CA1218080A - Procede de preparation de trifluoroethanol - Google Patents

Procede de preparation de trifluoroethanol

Info

Publication number: CA1218080A
Authority: CA; Canada
Prior art keywords: reaction; hydrogen; reactor; catalyst; volume
Prior art date: 1983-04-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000452375A

Other languages

English (en)

French (fr)

Inventor

Georges Cordier

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rhone Poulenc Specialites Chimiques

Original Assignee

Rhone Poulenc Specialites Chimiques

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-04-21

Filing date

1984-04-19

Publication date

1987-02-17

1984-04-19 Application filed by Rhone Poulenc Specialites Chimiques filed Critical Rhone Poulenc Specialites Chimiques

1987-02-17 Application granted granted Critical

1987-02-17 Publication of CA1218080A publication Critical patent/CA1218080A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims abstract description 48
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 44
239000001257 hydrogen Substances 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
239000003054 catalyst Substances 0.000 claims abstract description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 20
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 12
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052703 rhodium Inorganic materials 0.000 claims abstract description 11
239000010948 rhodium Substances 0.000 claims abstract description 11
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 11
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 10
239000007791 liquid phase Substances 0.000 claims abstract description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052697 platinum Inorganic materials 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims description 10
239000003245 coal Substances 0.000 claims description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
239000012071 phase Substances 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
229910052741 iridium Inorganic materials 0.000 abstract description 3
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
238000010926 purge Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
238000007086 side reaction Methods 0.000 description 4
230000009466 transformation Effects 0.000 description 4
UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000036647 reaction Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007872 degassing Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910000856 hastalloy Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229910001925 ruthenium oxide Inorganic materials 0.000 description 1
239000010959 steel Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000452375A 1983-04-21 1984-04-19 Procede de preparation de trifluoroethanol Expired CA1218080A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8306530A FR2544712B1 (fr)	1983-04-21	1983-04-21	Procede de preparation de trifluoroethanol
FR83.06530		1983-04-21

Publications (1)

Publication Number	Publication Date
CA1218080A true CA1218080A (fr)	1987-02-17

Family

ID=9288075

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000452375A Expired CA1218080A (fr)	1983-04-21	1984-04-19	Procede de preparation de trifluoroethanol

Country Status (9)

Country	Link
US (1)	US4533771A (de)
EP (1)	EP0125951B1 (de)
JP (1)	JPS6046102B2 (de)
AT (1)	ATE28182T1 (de)
BR (1)	BR8401817A (de)
CA (1)	CA1218080A (de)
DE (1)	DE3464593D1 (de)
ES (1)	ES531726A0 (de)
FR (1)	FR2544712B1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2638158B1 (fr) *	1988-10-21	1991-04-12	Rhone Poulenc Chimie	Procede de preparation de trifluoroethanol
US5629458A (en) *	1996-07-26	1997-05-13	Alliedsignal Inc.	Process for the preparation of 2 2 2 trifluoroethanol
EP1820789A1 (de) *	2006-02-13	2007-08-22	SOLVAY (Société Anonyme)	Verfahren für die Synthese von fluorierten Alkoholen

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2750263A (en) *	1951-10-05	1956-06-12	Oronzio De Nora Impianti	Apparatus for the reduction of organic compounds by hydrogenation
US2862977A (en) *	1956-12-21	1958-12-02	Du Pont	Hydrogenation of perfluoroalkanoic acids to 1, 1-dihydroperfluoroalkyl alcohols over ruthenium catalyst
US3180898A (en) *	1961-04-17	1965-04-27	Metallgesellschaft Ag	Process for the production of fatty alcohols by catalytic hydrogenation of fatty acids and their derivatives
BE755624A (fr) *	1969-09-02	1971-03-02	Hoechst Ag	Procede de preparation de 1,1-dihydro-perfluoro-alcanols
US4232170A (en) *	1979-01-31	1980-11-04	Allied Chemical Corporation	Process for homogeneous hydrogenation of esters
US4273947A (en) *	1979-01-31	1981-06-16	Allied Chemical Corporation	Hydrogenation of fluorine-containing carboxylic acids
US4255594A (en) *	1979-09-18	1981-03-10	Allied Chemical Corporation	Hydrogenation of halogen-containing carboxylic anhydrides
US4396784A (en) *	1980-06-24	1983-08-02	Phillips Petroleum Company	Hydrogenation of fluoroacids with rhenium-fluorided alumina catalyst

1983
- 1983-04-21 FR FR8306530A patent/FR2544712B1/fr not_active Expired
1984
- 1984-04-05 US US06/596,938 patent/US4533771A/en not_active Expired - Lifetime
- 1984-04-11 EP EP84400714A patent/EP0125951B1/de not_active Expired
- 1984-04-11 AT AT84400714T patent/ATE28182T1/de not_active IP Right Cessation
- 1984-04-11 DE DE8484400714T patent/DE3464593D1/de not_active Expired
- 1984-04-18 ES ES531726A patent/ES531726A0/es active Granted
- 1984-04-18 BR BR8401817A patent/BR8401817A/pt not_active IP Right Cessation
- 1984-04-19 CA CA000452375A patent/CA1218080A/fr not_active Expired
- 1984-04-20 JP JP59078772A patent/JPS6046102B2/ja not_active Expired

Also Published As

Publication number	Publication date
JPS59231032A (ja)	1984-12-25
DE3464593D1 (en)	1987-08-13
ATE28182T1 (de)	1987-07-15
US4533771A (en)	1985-08-06
FR2544712A1 (fr)	1984-10-26
ES8502072A1 (es)	1984-12-16
EP0125951B1 (de)	1987-07-08
FR2544712B1 (fr)	1986-01-10
EP0125951A1 (de)	1984-11-21
ES531726A0 (es)	1984-12-16
BR8401817A (pt)	1984-11-27
JPS6046102B2 (ja)	1985-10-14

Legal Events

Date	Code	Title	Description
2004-04-19	MKEX	Expiry

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CN101910100B (zh)	2014-01-08	由碳质原料生产醇的改进的方法
EP0005998B1 (de)	1982-05-05	Herstellung von Ameisensäure durch Hydrolyse von Methylformiat
US4417079A (en)	1983-11-22	Process for producing normal-octanol
EP0135436A1 (de)	1985-03-27	Verfahren zur Herstellung von linearen Olefinen aus Fettsäuren oder Estern von gesättigten Fettsäuren
US5841002A (en)	1998-11-24	Process for the commercial production of polyhydroxy alcohols and glycols
FR2460284A1 (fr)	1981-01-23	Procede de preparation de l'acetaldehyde
CA1218080A (fr)	1987-02-17	Procede de preparation de trifluoroethanol
EP0511126B1 (de)	1994-12-28	Verfahren zur Herstellung von Adipinsäure durch Hydrocarboxylierung der Pentensäuren
US2911422A (en)	1959-11-03	Synthesis of carboxylic acids from olefinic compounds, carbon monoxide and water in the presence of a solvent
FR2947264A1 (fr)	2010-12-31	Procedure de preparation de l'acide difluoroacetique
FR2458528A1 (fr)	1981-01-02	Procede d'homologation du methanol
FR2552424A1 (fr)	1985-03-29	Procede de preparation de 1,1,1,3,3,3-hexafluoropropane-2-ol par hydrogenolyse de l'hydrate d'hexafluoroacetone
US4602107A (en)	1986-07-22	Process for producing trycyclo[5.2.1.02,6 ]decane-2-carboxylic acid
EP0128059B1 (de)	1986-05-28	Verfahren zur Herstellung von 1,1-Dihydro-Perfluoralkanolen
US3445505A (en)	1969-05-20	Method of preparing a lower-alkyl-beta formylpropionate a n d related compounds
US4976947A (en)	1990-12-11	Process for the recovery of elemental iodine from alkyl iodides
FR2497794A2 (fr)	1982-07-16	Procede de production de l'acetaldehyde par carbonylation de l'ether-oxyde de dimethyle eventuellement en melange avec de l'acetate de methyle
FR2519628A1 (fr)	1983-07-18	Procede de preparation de l'ethylene glycol et de monoalcools inferieurs a partir du gaz de synthese en utilisant un nouveau systeme catalytique
FR2491458A1 (fr)	1982-04-09	Procede de preparation catalytique de l'acetaldehyde, par reaction de l'hydrogene sur l'anhydride acetique en phase liquide bouillante
EP0365403B1 (de)	1992-10-28	Verfahren zur Herstellung von Trifluoräthanol
FR2527598A1 (fr)	1983-12-02	Procede de preparation d'acide acetique en presence d'eau
FR2701944A1 (fr)	1994-09-02	Procédé d'hydroxycarbonylation de lactones en acides dicarboxyliques aliphatiques.
JPH06345688A (ja)	1994-12-20	エステル類の製造方法
JP2022079247A (ja)	2022-05-26	第２級アルコールの製造方法
FR2701945A1 (fr)	1994-09-02	Procédé de carbonylation des buténols allyliques et de leurs esters.